(1R,2r)-boc-2-氨基环己烷羧酸 | 233661-54-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (1R,2r)-boc-2-氨基环己烷羧酸
• 中文别名: (1R,2R)-BOC-氨基环己烷羧酸；(1R,2R)-2-叔丁氧羰基氨基环己烷羧酸
• 英文名称: (1R,2R)-2-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylic acid
• 英文别名: trans-2-((tert-Butoxycarbonyl)amino)cyclohexanecarboxylic acid；(1R,2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohexane-1-carboxylic acid
• CAS: 233661-54-6
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: QJEQJDJFJWWURK-RKDXNWHRSA-N

物化性质

• 沸点：
  396.7±31.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2924299090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (1R,2r)-boc-2-氨基环己烷羧酸 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 (1R,2R)-2-氨基环己甲酸
  参考文献：
  名称：

  Structure−Activity Studies of 14-Helical Antimicrobial β-Peptides:  Probing the Relationship between Conformational Stability and Antimicrobial Potency

  摘要：

  Antimicrobial a.-helical a-peptides are part of the host-defense mechanism of multicellular organisms and could find therapeutic use against bacteria that are resistant to conventional antibiotics. Recent work from Hamuro et al. has shown that oligomers of beta-amino acids ("beta-peptides") that can adopt an amphiphilic helix defined by 14-membered ring hydrogen bonds ("14-helix") are active against Escherichia coli [Hamuro, Y.; Schneider, J. P.; DeGrado, W. F. J. Am. Chem. Soc. 1999, 121, 12200-12201]. We have created two series of cationic 9- and 10-residue amphiphilic beta-peptides to probe the effect of 14-helix stability on antimicrobial and hemolytic activity. 14-Helix stability within these series is modulated by varying the proportions of rigid trans-2-aminocyclohexanecarboxylic acid (ACHC) residues and flexible acyclic residues. We have previously shown that a high proportion of ACHC residues in short beta-peptides encourages 14-helical structure in aqueous solution [Appella, D. H.; Barchi, J. J.; Durell, S. R.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 2309-2310]. Circular dichroism of the beta-peptides described here reveals a broad range of 14-helix population in aqueous buffer, but this variation in helical propensity does not lead to significant changes in antibiotic activity against a set of four bacteria. Several of the 9-mers display antibiotic activity comparable to that of a synthetic magainin derivative. Among these 9-mers, hemolytic activity increases slightly with increasing 14-helical propensity, but all of the 9-mers are less hemolytic than the magainin derivative. Previous studies with conventional peptides (a.-amino acid residues) have provided conflicting evidence on the relationship between helical propensity and antimicrobial activity. This uncertainty has arisen because alpha-helix stability can be varied to only a limited extent among linear alpha-peptides without modifying parameters important for antimicrobial activity (e.g., net charge or hydrophobicity); a much greater range of helical stability is accessible with beta-peptides. For example, it is very rare for a linear alpha-peptide to display significant a-helix formation in aqueous solution and manifest antibacterial activity, while the linear beta-peptids described here range from fully unfolded to very highly folded in aqueous solution. This study shows that beta-peptides can be unique tools for analyzing relationships between conformational stability and biological activity.

  DOI：

  10.1021/ja0270423
• 作为产物：
  描述：

  (1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid 在 sodium hydroxide 、 乙酰氯 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (1R,2r)-boc-2-氨基环己烷羧酸
  参考文献：
  名称：

  对映体纯 β-氨基酸：方便获得反式-2-氨基环己烷甲酸的两种对映体

  摘要：

  对映体纯的反式-2-氨基环己烷甲酸是螺旋β-肽的重要组成部分。我们在这里报告说，这种氨基酸可以通过简单的一锅法从反式环己烷-1,2-二羧酸以良好的收率获得，包括环化成酸酐，用氨形成酰胺，以及随后的霍夫曼型降解苯碘（III）双（三氟乙酸盐）（PIFA）作为氧化剂。通过分别用 Fmoc-OSu 和 BOC2O 处理氨基酸获得 N-Fmoc-和 N-BOC-保护的衍生物。N-BOC 衍生物可以通过直接从反式-环己烷-1,2-二羧酸到 N-BOC 保护的氨基酸的一锅法制备，以更高的总产率制备。起始反式 1 的两种对映异构体，通过使用（R）-或（S）-1-苯乙胺分离市售的外消旋反式-1,2-环己烷二甲酸，可以容易地大量获得2-环己烷二甲酸。从 (R)-1-苯乙胺获得的非对映异构纯盐的 X 射线晶体学显示，二酸组分的构型是 (1R,2R)，而不是文献中报道的 (1S,2S)。(© Wiley-VCH Verlag

  DOI：

  10.1002/1099-0690(200209)2002:17<2948::aid-ejoc2948>3.0.co;2-e

文献信息

• TERTIARY AMINE COMPOUND OR IMINE COMPOUND-POLYMER CONJUGATE AND PRODUCTION METHOD THEREFOR
  申请人：Seikagaku Corporation

  公开号：US20200138964A1

  公开（公告）日：2020-05-07

  Provided is a compound obtained by conjugating a tertiary amine compound or imine compound, which is useful as a drug, with a polymer, in which a structure D + having a quaternary ammonium salt or iminium salt formed from a tertiary amine compound or imine compound D and a polymer residue Poly having a carboxy group are bonded to each other via a structure —C(R 1 )(R 2 )OC(O)ANHC(═O)—.

  提供的是一种化合物，通过将一种三级胺化合物或亚胺化合物与聚合物共轭，用作药物，其中具有由三级胺化合物或亚胺化合物D形成的季铵盐或亚胺盐的结构D + 和具有羧基的聚合物残基Poly通过结构—C(R 1 )(R 2 )OC(O)ANHC(═O)—相互键合。
• [EN] SELECTIVE CALCIUM CHANNEL MODULATORS<br/>[FR] MODULATEURS SÉLECTIFS DES CANAUX CALCIQUES
  申请人：ZALICUS PHARMACEUTICALS LTD

  公开号：WO2011032291A1

  公开（公告）日：2011-03-24

  Methods and compounds effective in ameliorating conditions characterized by unwanted calcium channel activity, particularly unwanted T- type calcium channel activity are disclosed using a series of compounds containing N-acylated cyclic amines linked to an aπl ring as shown in formula (I).

  揭示了一种使用一系列含有N-酰化环氨基与aπl环相连的化合物来改善以不需要的钙通道活性为特征的状况的方法和有效化合物，特别是不需要的T型钙通道活性。
• Ribosomal incorporation of cyclic β-amino acids into peptides using <i>in vitro</i> translation
  作者：Joongoo Lee、Rafael Torres、Do Soon Kim、Michelle Byrom、Andrew D. Ellington、Michael C. Jewett

  DOI：10.1039/d0cc02121k

  日期：——

  We demonstrate in vitro incorporation of cyclic β-amino acids into peptides by the ribosome through genetic code reprogramming. Further, we show that incorporation efficiency can be increased through the addition of elongation factor P.

  我们证明了通过遗传密码重编程在核糖体中将环状β-氨基酸掺入肽中。此外，我们显示可以通过添加延伸因子P来提高掺入效率。
• Method for delivery of molecules to intracellular targets
  申请人：——

  公开号：US20030119189A1

  公开（公告）日：2003-06-26

  Disclosed are &bgr;-peptides and &bgr;-peptide conjugates that are capable of diffusing or otherwise being transported across the cell membranes of living cells. The &bgr;-peptides contain at least six &bgr;-amino acid residues, at leastsix of which are preferably &bgr; 3 -homoarginine residues. It has been found that when pharmacologically-active agents are conjugated to these types of &bgr;-peptides, the resulting conjugates (also disclosed herein) are also capable of diffusing or otherwise being transported across the cell membranes of living cells, including mammalian cells.

  揭示了能够扩散或以其他方式被运输穿过活细胞细胞膜的β-肽和β-肽共轭物。这些β-肽包含至少六个β-氨基酸残基，其中至少有六个是优选的β3-同型精氨酸残基。已经发现，当药理活性剂与这些类型的β-肽结合时，所得到的共轭物（本文中也披露）也能够扩散或以其他方式被运输穿过活细胞细胞膜，包括哺乳动物细胞。
• Parallel assembly of dipolar columns composed of a stacked cyclic tri-β-peptide
  作者：Futoshi Fujimura、Makoto Fukuda、Junji Sugiyama、Tomoyuki Morita、Shunsaku Kimura

  DOI：10.1039/b600407e

  日期：——

  A novel cyclic trimer of a β-amino acid, trans-2-aminocyclohexylcarboxylic acid, was synthesized and its conformation and ability to form assemblies investigated. FT-IR and NMR measurements and computational calculations showed that this cyclic tri-β-peptide has a C3-symmetric conformation with trans amide groups. A notable feature of the conformation is a vertical and parallel orientation of the three amide groups to the cyclic skeleton. The cyclic tri-β-peptide was crystallized from a solution in trifluoroacetic acid–methanol (or trifluoroacetic acid–water) to yield a rod-shaped molecular assembly, as observed by TEM. The electron crystallography of the rod-shaped assembly both in suspension and in ultrathin cross-section revealed that the cyclic tri-β-peptides were stacked up to form molecular columns, and that a two-fold screw symmetry operation along the column direction was present in the unit cell, which contained two cyclic tri-β-peptides. This indicates that all the amide groups are oriented in the same direction. Since any two molecular columns are staggered by a quarter of a c-axis length and aligned parallel to each other, the dipole moments of the columns are aligned to enhance the strength additively in the whole assembly.

  我们合成了一种δ-氨基酸的新型环状三聚体--反式-2-氨基环己基羧酸，并研究了它的构象和形成集合体的能力。傅立叶变换红外光谱和核磁共振测量以及计算表明，这种环状三δ肽具有反式酰胺基团的 C3 对称构象。该构象的一个显著特点是三个酰胺基团与环状骨架的垂直和平行取向。环状三δ肽在三氟乙酸-甲醇（或三氟乙酸-水）溶液中结晶后，经 TEM 观察，生成了棒状分子组装体。对棒状组装体的悬浮液和超薄横截面进行电子晶体学分析后发现，环状三牺²肽堆叠在一起形成分子柱，在包含两个环状三牺²肽的单元胞中，沿分子柱方向存在两重螺旋对称操作。这表明所有的酰胺基团都朝向同一方向。由于任何两个分子柱都错开了四分之一的 c 轴长度并相互平行排列，因此分子柱的偶极矩排列在一起，从而增强了整个组装体的叠加强度。